Most Beautiful Towns in Tuscany

There are loads of towns in Tuscany. And most of them would certainly qualify as beautiful. Some are large towns such as Siena which is quite well-known. Others are quaint villages and maybe not a town you’ve heard of such as Casole d’Elsa— which you’ll find out about soon enough. Admittedly, Tuscany is über popular. Finding beautiful towns is easy but finding a beautiful town that’s not so touristed is a bit more difficult. I visited San Gimignano on my third visit to Tuscany. I resisted because it’s on every tourist’s itinerary. But I wanted to see what all the fuss was about. While I did think it was beautiful, I thought other towns were equally so and less kitschy. However, I always say that each person has to travel her own way — to find the places that resonate with you that YOU want to visit.
This town is 12km east of Lucca —a bigger and more popular town that is also worthy of spending time. But Montecarlo will get you away from the crowds. Now this is not a town loaded with sites. What you’ll find in Montecarlo is that slow, steady Italian — specifically Tuscan — way of life. And, personally, I love wandering about towns where it’s mostly Italians going about their daily lives. This walled city does have a few reasons to visit though. The first is a fortress, known as the Rocca del Cerruglio, that was built between the 14th and 16th centuries that still stands and is quite impressive. It’s composed of a main, semicircular-shaped tower — called the masito — and 2 square shaped towers — Torre dell’Apparizione and the Torre di Santa Barbara tower — which all form a grand triangular structure. There are also a few churches worthy of some time with the Pieve di San Pietro being the most interesting.
I think the province of Arezzo is often overlooked by travelers to Tuscany. This is the province to the east of Siena that contains the provincial capital of Arezzo as well as Cortona of Frances Mays’ fame (Under the Tuscan Sun). There are loads of gorgeous towns and villages here. Poppi sits in the gorgeous Castentino Valley and is part of the National Park of Foreste Casentinesi. This town in Tuscany is striking from a distance with the Castle dei Conti Guidi commanding your attention. And you’ll definitely want to check out that castle. The construction of the “current” castle began around 1260. Love the word “current” there. Like 1260 was just a few years ago! Anyway… Castle dei Conti Guidi has undergone many changes over the years — extensive renovations and expansions.
There’s a beautiful chapel in the castle — The Chapel of the Counts Guidi — that is one of the most stunning rooms in the castle. Frescoes are also the star attraction here with the stories of the Gospels painted by Taddeo Gaddi, a student of Giotto. And the library is spectacular with quite the collection. Really, you won’t want to miss spending some time in this beautiful castle. Because it’s Italy, you’ll find churches and abbeys. And Poppi has the Romanesque Abbey of San Fedele, the Church of San Marco and the Church of the Augustinians which are all worth a quick look at the very least. You always want to at least poke your head in the churches in Italy because you never know what beautiful piece of artwork you might see. The Casentino region is known for its traditional menus so this means Poppi has some fabulous places to eat fresh, local food. There are a few places to stay in town but again, this is Tuscany, so finding an agriturismo in the countryside just outside of town might be easier. Poppi really is one of the most beautiful towns in Tuscany. Don’t miss it!